Collective Synthesis and Biological Evaluation of Tryptophan-Based Dimeric Diketopiperazine Alkaloids
| Autor: | Shinji Tadano, Sachiko Tsukamoto, Yukihiro Sugimachi, Hayato Ishikawa, Michinori Sumimoto |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
chemistry.chemical_classification
Protease Aqueous solution 010405 organic chemistry Stereochemistry Chemistry medicine.medical_treatment Alkaloid Organic Chemistry Tryptophan General Chemistry Ditryptophenaline 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Amino acid medicine Asperdimin Biological evaluation |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 22(4) |
| ISSN: | 1521-3765 |
| Popis: | A concise two one-pot synthesis of WIN 64821, eurocristatine, 15,15'-bis-epi-eurocristatine, ditryptophenaline, ditryptoleucine A, WIN 64745, cristatumin C, asperdimin, naseseazine A, and naseseazine B is detailed, based on a unique bioinspired dimerization reaction of tryptophan derivatives in aqueous acidic solution and a one-pot procedure for the construction of diketopiperazine rings. Total yields of these alkaloid syntheses were from 10 up to 27 %. In addition, 1'-(2-phenylethylene)-ditryptophenaline was synthesized by using three one-pot operations. The studies detailed herein provided synthesized natural products for inhibitory activities of ubiquitin-specific protease 7 (USP7) and foam cell formation in macrophages. The newly listed biological evaluation for tryptophan-based dimeric diketopiperazine alkaloids discovered 15,15'-bis-epi-eurocristatine, 1'-(2-phenylethylene)-ditryptophenaline, and WIN 64745 as new drug candidates. |
| Databáze: | OpenAIRE |
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